My Favorite Coaching Questions (Part I)

I have wanted to be a coach ever since I was 16. I wasn’t good enough at the time to play varsity sports at my high school of over 4,000 students, so I decided to do the next best thing…coach. I volunteered to coach Little League basketball and baseball. It was a ball!

Not long after that, I thought I might want to start a career as an athletic coach. My school, Tulane University, had a teacher/coach degree program. Perfect, I thought.

My father thought otherwise. He suggested I could come home to Miami, attend a local community college, and get that education. He said he was paying too much for tuition at a prestigious private school so I could graduate with a teaching degree. There went my coaching career, at least for the time being.

Flash forward to today. I have been coaching CEO’s and small business owners now for over twenty years. Hundreds of them. Funny how things turn out.

Over this period, I have received extensive coaching training and have read many books. As a result, I have assembled a powerful collection of coaching questions. I will share some with you this month and save the remaining questions for next month’s newsletter.

As a small business owner/executive, you are a coach by default. If you have employees, one of your most important responsibilities is to coach your team members to achieve desirable results. Even beyond your own employees, you will find yourself coaching clients, vendors, and friends. In his popular TED Talk, Dr. Atul Gawande makes a compelling case for both the need to coach and to be coached.

I hope you enjoy and benefit from using the following coaching questions.

  1. What if you did know?

Sometimes I will ask a client a question, and the response will be “I don’t know”. While the client may not know the exact answer, I am fairly certain that he has at least a good guess. So I will then ask this question as a follow-up and will almost always get a good answer.

  1. Would you rehire that employee?

The decision to retain or fire an employee is tough to make for any CEO. Sometimes the executive takes an inordinate amount of time to make this decision, whether it is a performance issue or a behavioral problem. This question I find helps the executive decide. Would you in fact, rehire the same employee in the future? FYI, the answer is usually “no”.

  1. It’s a year from now, and your decision has turned out terribly. What went wrong?

Hopefully, most of your decisions go right. When we are considering the outcomes of our decisions, we typically do a post-mortem. We wait until the decision plays out, then evaluate it. This question forces us to consider the negative consequences of a decision before our actions and the miscalculations that might have contributed to it.

  1. How do your core values speak to this decision?

Strategic decision-making is difficult. Whether it is a hiring/firing decision, a capital allocation decision, or maybe a key marketing decision, these decisions are tough for any executive. They are even tougher without a set of written core values. The core values serve as a filter or a “north star” for each of these decisions. As an example, if one of your company’s core values is “integrity”, you have a pretty easy decision to make if an employee is stealing. Applying your core values to your decisions makes those decisions much easier.

  1. What is your blind spot on this decision?

Blind spots often cause car accidents. I can’t see that car coming up on my right passenger side until it is too late. Bam! Likewise, every small business owner has blind spots. Information, data, or experiences that we can’t see or think of at the time of a decision. Posing this question, the coach is asking the executive to consider what those blind spots might be. What information are you missing that would make this decision easier?

Next month, I’ll share the remaining five questions. Have fun trying these out in the meantime.

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